


Roll for Insight

by K_K_TiBal



Category: Supernatural
Genre: Alternate Universe - Tabletop Gaming, Demiromantic Castiel, Demisexual Castiel, Dungeons and Dragons, Friends to Lovers, Love Confessions, M/M, Roleplay
Language: English
Status: Completed
Published: 2016-04-26
Updated: 2016-04-26
Packaged: 2018-06-04 15:46:16
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,021
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6664648
Author URL: https://archiveofourown.org/users/K_K_TiBal/pseuds/K_K_TiBal
Summary: <blockquote class="userstuff">
              <p>Dean and Cas are a part of the same Dungeons and Dragons campaign and Dean's character keeps flirting with Cas's character. Just the characters though. This is all just a game.</p>
            </blockquote>





	Roll for Insight

**Author's Note:**

> I've been getting into DnD. So now Dean and Cas are, too.

“Alright, you all arrive at a bar called ‘The Rusty Goblet’ and walk inside.”

Charlie leaned forward and looked over Ash, squinting her eyes in concentration. “What do we see?”

Ash cleared his throat and began to gesture animatedly as he described the scene around them. Dean didn’t envy the job Ash had at improvising their surroundings and characters, though apparently Ash thrived on it. 

“You see a bartender on the other side of the bar, cleaning some mugs. He’s a big fellow that looks at you all suspiciously. There’s actually quite a few customers here and there and a musician playing some sweet-ass tunes in a corner of the room. It’s a little bit noisy with the sound of rambunctious laughter and music.”

“Dibs on the bard!” yelled Jo. 

Ash rolled his eyes. “For the last time, Jo. You can’t call dibs. Just go talk to him.”

Dean snickered as Jo huffed, but she was new to playing Dungeons and Dragons, so no one minded the rules being explained to her over again. 

Charlie had actually been the one to invite him to play a campaign last year and while he’d originally been hesitant about it, DnD was easily what he looked forward to the most every week. They’d ended their last campaign about a month and a half ago and with the start of this new one, Dean and Sam had brought their friend Jo who’d expressed interest in playing - and Charlie had brought a new guy named Castiel. 

Dean glanced over at the guy, combing his eyes over his features as Castiel stared intently at their Dungeon Master.

Castiel seemed a little odd. Bookish. He was always wearing a button-up shirt when they gathered to play on Sunday nights as opposed to everyone else’s more casual look, but when he finally opened up he was fun enough to talk to and role-play with. Plus, his Celestial Aasimar character was pretty freaking cool. 

“Alright,” Ash continued, “You’re in the bar. What do you do?”

“I’m gonna go up to the counter,” Dean announced, “and sit down. Then I’m going to ask the bartender how much a drink around here is.” 

“That’ll be five gold.” Ash ducked his head and made his voice gravelly as he attempted to speak in the voice of the character. 

Dean gaped. “Are you kidding? That’s so - wait, wait, no, I don’t actually say that. Okay, so I wink at him -” 

Jo, Sam, and Charlie all groaned in unison. 

“-  _ I wink at him  _ and say ‘Are you sure?’ Wait, can I do an insight roll on him to see if he’s into dudes?”

Ash shrugged. “Go for it.”

Dean picked up his twenty sided-die and rolled it, groaning at the number. “Four.”

Ash grinned. “You have no idea about this man’s sexuality, but after the way his face darkens after the wink… you get the sense he doesn’t appreciate it.  _ And _ he tells you the price is now six gold pieces.”

Dean harrumphed as Castiel chuckled next to him. 

“I also go up to the bar,” Castiel said, “And pay ten gold for two drinks, giving one to Michael.” 

That was easy for him to buy, seeing as his character had a shit-ton of wealth that came with his royal bloodline.

Sam cleared his throat. “I’m going to--”

“I do an insight check to see if Emmanuel is into dudes!” Dean interrupted.

Everyone apart from Castiel had joined in on the groaning. So  _ maybe _ Dean did this particular insight check a little more often than necessary. And maybe a little more often on Castiel’s character. But if he could just roll high enough he wouldn’t  _ have  _ to make it all the time. Besides, if he could somehow seduce Emmanuel, he could potentially gain some of his gold. 

Dean blew on the dice and rolled it across the table, landing on the number seven. 

“You can’t tell his sexuality.” Ash said and rubbed at his eyes. “Jo? You’re gonna go talk to the bard, right?” 

“And Ruby goes to follow her.” Sam added, referring to the Tiefling character that he was currently playing.

Jo nodded enthusiastically while Castiel shot Dean a small shrug with a smug smile. 

“Why don’t you ever roll to see if  _ my _ character is into dudes?” Dean muttered.

“Because literally all of us can tell how fucking bisexual both you and Michael are, Dean. You’re not hiding it,” Charlie said as she cupped the dice in her hand. 

“Besides,” Castiel murmured in a low voice, “Emmanuel has a high enough natural perception that he could easily tell. Michael would be better off just making a move on him.”

Dean huffed and crossed his arms over his chest, but the guy had a point. Too bad that was going way too into taboo territory for him. There was a difference between roleplaying in a game and letting someone know that he might actually be interested in him by accidentally having character bleed. 

“As you walk over to the other side of the room, the door to the front of the bar bursts open,” Ash banged on the table with the palm of hand, interrupting their banter. “And a man with a slash on his face looks around wildly saying ‘Help! Anyone! My daughter’s been kidnapped! Can anyone help me?’” 

Dean sat up a little straighter at the introduction of the quest and began tossing his die back and forth between his hands. Glancing around him, he saw Cas looking back and forth between him and Ash. Cas’s character had a soft spot for children in distress, which made Dean squint at Ash suspiciously. This was obviously created with Emmanuel in mind. 

Castiel licked his lips and cleared his throat. “I walk up to the man and ask what’s happened.”

“I follow him.” Dean said immediately, only blushing a little when Cas smiled at him. 

“Did I hear him say that?” asked Sam.

Ash raised an eyebrow. “Everyone roll for perception to see if you heard him with the exception of Castiel and Dean who were in the front of the bar and could clearly hear and see him.”

There was a sound of complete silence followed by the tapping of die rolling across the table. 

“Two.”

“Seven.”

“One.”

Ash snorted as the low rolls were begrudgingly announced. “Man, sure is loud in here, isn’t it? Jo and Sam’s characters are too busy listening to the minstrel to hear anything, and Charlie? Gilda is distracted by all of the food.”

“Dammit,” she muttered. 

“So Emmanuel and Michael are the only ones to notice this man.” Ash hunched over and pressed a hand to his face as his voice changed to fit the character. “Please! My daughter was just kidnapped! The guards don’t believe me. Can you help?”

“Of course,” Castiel said confidently and looked over at Dean. “We’ll do whatever we can. Could you tell who took her?”

“It looked like an orc, but I can’t be sure.”

Dean bristled on behalf of his character at the mention of the orc. It just so happened that Michael had a bad background that involved orcs. 

“Right. Should we go and get the rest of our team?” Dean asked, looking up at the other three. 

“No time!” Ash threw his hands in the air and mimed tugging on their arms. “Hurry, please!”

Dean looked over at Castiel and shrugged. “Alright, lead the way.”

“The man races back out of the bar and into the dark street, urging you to follow. What do you do?” 

“I follow him,” Castiel said emphatically.

Dean squinted suspiciously as Ash gazed at him serenely. This was all getting just a little too fishy for his taste. It was like it was a quest that was perfectly crafted for just the two of them to take on. 

“I guess I’ll follow Emmanuel,” he said after a moment, not wanting Castiel’s character to have to face something alone. 

“The man races into an alleyway and you hear him yell “Quickly, they went this way!’ As soon as you enter the alleyway behind him, he turns and smiles. You each feel a blow on the back of your heads and are rendered unconscious.”

_ “What?”  _ Castiel stood up with his eyebrows raised. “I don’t even get to have a reaction?”

“Nope.” Ash smirked and began rolling a smaller die. “Emmanuel takes six bludgeoning damage and Michael takes...nine.”

Dean grumbled as he subtracted the damage from his hitpoints. Damn, it had been stupid of them to fall for something that obvious. He’d known something was off.

“You should have rolled for insight.” Ash said with a wink. “It wouldn’t have taken a super high roll to see if he was lying.” 

Castiel huffed and slumped back down with his arms over his chest. 

“You both wake up in a dark room with your hands tied behind your back. Now we’re going to pause for just a second becaaaaause…”

Sam grinned and looked over at Jo and Charlie. “Because now it’s a side quest. You’ve got to go into a separate room from us.”

Ash wiggled his eyebrows as he walked across the room and pulled open the door to his bedroom. 

In times where the group got separated enough to the point where they were having entirely different storylines, one group got banished to Ash’s bedroom and they took turns having their Dungeon Master walk them through the plotline. Charlie had explained how it worked the first time Dean played; it was all about making sure there wasn’t an unfair advantage, or metagaming. 

So far it hadn’t happened yet in this new campaign, but now… now, Dean was going to be both metaphorically and physically trapped in a room with a guy he was harboring the  _ hugest _ crush on. 

Both Dean and Cas stood up with their dice in hand, with Dean turning back to glare at the rest of the group, who only smiled at him widely. Charlie was the exception; she was making obscene hip-thrusting motions. 

Dean flushed violently and turned back around, shuffling into the room with Cas. 

“Alright, I’ll get to you two as soon as I give the others a chance to roleplay a little.” Ash wiggled his fingers and winked at the two of them as he closed the door behind them. 

Castiel cleared his throat and gingerly sat down on the edge of the bed. “That was pretty dumb of us, wasn’t it?”

Dean shrugged and sat down next to him. “Probably. But we were acting in character and that’s what matters.”

Castiel hummed and smiled after a few moments, clearly still assessing the fictional situation while Dean was assessing a more real one. “This almost makes me wish I’d decided on a race that could shape shift.Then I could shift into some other creature and out of the ropes.” 

“Nah, man. Your Aasimar is badass. Part celestial being? It fits you.” Dean averted his eyes and coughed when he realized what he’d said. 

Castiel ducked his head. “So… what do you think happened?”

Dean mulled over the last five minutes in his head and licked his lips at the obvious realization. 

This had been planned. All of it.

The quest was designed to lure them out specifically. Had they all actually rolled low numbers? Dean had just taken their word for it. And now here they were, separated from the rest of the group…

Those fuckers. 

“I think they did it on purpose.” Dean muttered, glaring at the door as if it would somehow bore a hole through it. 

“What?” Castiel tilted his head curiously. 

“The - quest. They totally separated us on purpose.” 

Castiel hummed and folded his hands together in his lap.“Now that you mention it, the man did seem oddly focused on -”

“No, Cas. Not in the game.” 

Castiel furrowed his brows together. “What do you mean?”

The door swung open  and Ash cleared his throat loudly before stepping into the room and shutting the door behind him. “Evening, gentlemen. Ready to get back to the game?”

They both nodded and Ash clapped his hands together. “Perfect. So we left off with you two tied up in a darkened room.”

“Alright,” Dean muttered. “Describe what’s going on a little more.”

“Right. You’re both wrapped very tightly in rope and chained to a wall on opposite sides of the room. Emmanuel’s wings are also tied tightly to his body. It’s dark but you can tell the room isn’t that big. Emmanuel can especially tell the size, seeing as he had better vision. As you begin to look around the best you can, you hear a booming voice echo in your minds. ‘ _ The secrets will set you free’  _ is what it says.”

“The secrets?” Castiel asked curiously. 

“The secrets.” 

Castiel looked over at Dean who simply shrugged. It didn’t make any sense to him either. 

“Do you have any secrets, Michael?” Castiel asked with a small tilt to his head. 

Dean made his voice a little more gravely. “Secrets? Of course. Who doesn’t?”

“Who indeed. I wonder who would kidnap us for secrets.”

Dean shot Ash a look; he was remaining suspiciously impassive about everything. 

Castiel appeared to chew on the inside of his cheek before staring up at the ceiling. “I once stole a sword from my father’s armory.” He peeked over at Ash. 

“You feel the ropes around you grow marginally looser. Not by much, but enough to notice.”

Oh. Interesting. 

“I stole a pie?” Dean tried out.

“Your ropes loosen less than Emmanuels, but they still do loosen.”

Castiel raised an eyebrow. “The better the secret the looser the bonds get.”

Dean sucked in a breath and mentally dug through his character’s backstory, trying to decide which secrets he could share. “When I first learned to rage, I accidentally hurt a man from my village.” 

“The ropes no longer feel incredibly restricting. Breathing is a lot easier.”

“I detest my parents and the pressure they put on me to succeed them.” Castiel immediately shot back.

They spent the next few minutes swapping small secrets as the ropes around them grew looser until finally they fell away completely. 

“Your arms are still chained to the wall,” Ash reminded them, “and there is no visible way out of the room yet.” 

Dean leaned forward and clenched his fists together. “My mother died in a fire because I was careless.”

“The chains fall from of your wrists and you can now walk around the room.”

“Okay, I immediately go over to Cas - uh, Emmanuel,” Dean corrected, “and investigate his chains.” 

Ash gestured as his die. “Roll for investigation.”

“No, no. I’ll just give up another secret.” Castiel said like it was obvious and hummed as he thought of another possibility. He cleared his throat and Dean noted that his voice dropped in pitch as he spoke again. “I don’t fall in love often. People think I’m odd because of it.”

Dean turned to look at Cas, who was chewing on his lip and looking down at his hands. “That’s not something to be ashamed of.”

“The chain unlocks and falls away,” Ash chimed in. 

Castiel shrugged. “Regardless, it worked.” 

Yeah, but they were still trapped in the room with no obvious way out. Knowing Ash, they probably wouldn’t be able to get out unless one of them gave up something huge. Dean took a deep breath and rested a hand on the bed next to Castiel, causing him to look up and lock eyes. 

“I like you,” he murmured. “A lot. But we’re friends. Teammates. I’m scared of - of messing that up.” 

A pink tinge crawled up Castiel’s neck as his eyes widened. “I - I like you, too. I think you’re… wonderful. A… great fighter, and equally as intelligent.”

It was Dean’s turn to blush. “Nah, I’m - it’s nothing.”

“You  _ are _ though. A great tactician. I enjoy being with you, Dean.” Castiel froze, then clapped a hand over his mouth. “Michael. Apologies, I meant Michael.”

A small smile creeped into the corner of Dean’s mouth as he stared into Castiel’s mortified eyes. “I enjoy being with you too, Cas.” 

They stared at each other for what felt like a lot longer than what was most likely just a few seconds, just allowing themselves to be absorbed in each other’s gaze. 

“Holy  _ fuck.  _ Okay, the door fucking opens, you’re free and shit,  _ now just fucking kiss already!” _ They looked over as Ash threw his hands up into the air and stood up in a huff. He yanked the door back open and yelped as Charlie, Jo, and Sam all tumbled into the room after apparently losing their balance against the door. 

“Did they do it, yet?” Charlie asked.

Dean stood up and nudged at them with his foot. “Everyone out. Go on. Get the fuck out.” 

Ash clicked a finger gun at the two of them as Jo smiled widely while she tugged the rest of them out of the room. Once the rest of the group was effectively out of their presence, Dean shut the door loudly and turned back to Cas, whose face was currently a bright red. 

“So,” Dean said, trying to remain suave, “You enjoy me.” 

Castiel managed an eyeroll and motioned for Dean to sit back down next to him. “I might.”

Dean chucked and sat on the corner of the bed, much closer in proximity to Cas than he’d been the first time. “You might?”

Dean’s heart skipped a beat as Castiel’s eyes flicked down to his lips. “Roll for insight,” he murmured. 

“You know how terrible I am at insight rolls,” Dean objected, but he was already reaching for his die from his pocket. It was hard to concentrate with Cas being so close to him. Finally, after a brief moment of frustration, the die went rolling across the blanket until it finally came to a stop. 

Dean glanced up just in time to see Cas smile and close the distance between them, warm lips pressing up against his own in a moment of pure elation. 

A natural twenty. 


End file.
